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The Simpsons (Classic): “Sideshow Bob Roberts”

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“Sideshow Bob Roberts” (season six, episode five; originally aired 10/9/1994)

Satire is nothing without a target, but good satire fixes its aim on multiple, moving targets. One-sided sendups of political philosophies or social movements end up stinking of agenda, forever dogged by the impression that the author is trying to sway as well as inform and entertain. Besides, limiting the targets of a satire is, by extension, setting a limit for the amount of jokes you can tell. Let us all learn from the mistakes of Fox News’ short-lived Daily Show clone, The 1/2 Hour News Hour. (You get it? It’s called that because some namby-pamby liberals gave the other 30 minutes away to people who hadn’t earned it.)


Technically, “Sideshow Bob Roberts” saves its greatest reserves of comedic contempt for a single entity—but it’s an entity that represents multitudes. The subjects of the episode’s most effective political takedowns aren’t Republicans (though their local headquarters is portrayed as a dreamhouse from the Universal backlot circa Frankenstein) or Democrats (this in spite the fact that Springfield’s resident “Spendocrat” dynamo, Mayor “Diamond” Joe Quimby, willingly admits to all questions of his character save for illiteracy—and even that’s a recent development). No, the group that takes it on the chin most vigorously in this, The Simpsons’ finest half-hour of political satire, is the American voting public.

In its heyday, the writers of the Simpsons loved whipping a group of people into a fury for the smallest reasons. In “Sideshow Bob Roberts,” the angry mob masquerading as the population of Springfield has no qualms with a thrice-convicted felon running for mayor. In fact, with a little wheel-greasing from conservative blowhard Birch Barlow (a dead-on Rush Limbaugh caricature voiced by Harry Shearer) and pandering from Candidate Terwilliger, the voters are quite eager to have someone with Sideshow Bob’s criminal record running against Quimby. In a prescient echo of the way the real world was leaning at the time, “Sideshow Bob Roberts” first aired a month before the 1994 U.S. Congressional elections, which saw Republicans seizing houses of the Congress—gaining the majority of seats in the House of Representatives for the first time since the 1950s. Clearly, the American people animated and non-animated were secretly longing for leaders who would, to paraphrase Bob, lower taxes, brutalize criminals, and rule them like a king.


To the naked eye, this might seem like The Simpsons writing itself with its left hand only, but “Sideshow Bob Roberts” is an equal-opportunity offender. Its titular character may conduct himself as if he and he alone is fit to occupy the corridors of power, but his opponent in the mayoral race acts as if he doesn’t have to do anything to keep his job. Like his counterparts in the House of Representatives circa ’94, Quimby is flabby and content in his capacity as mayor, his rampant corruption and public buffoonery spawning Birch Barlows like a gremlin dipped into an elephant-shaped swimming pool. (A swimming pool its owners are desperately hoping turns into a time machine to 1963.) “Diamond Joe” makes no real attempts at courting the vote: His big campaign ad is a parade of mediocre achievements that ends with the tagline “If you were running for mayor, he’d vote for you”; it requires the actions of Lisa and Bart to score points for Quimby during an easy-slam-dunk photo op at Springfield Elementary.

Most remarkably, “Sideshow Bob Roberts” grounds itself deep in political satire and electoral history—I caught the allusions to Watergate and the televised Kennedy-Nixon debate, but I definitely wasn’t looking for echoes to the 1988 campaign between George H.W. Bush and Michael Dukakis—while simultaneously staging the latest bout in Bart and Bob’s ongoing game of Road-Runner-and-Coyote. Bob’s plan for revenge is particularly circuitous this time around, and it doesn’t leave much room for the usual barely veiled threats and persistent menace of Kelsey Grammer’s past appearances. In a brilliant use of the show’s campaign-trail plotting, Bob leaves his intimidation tactics to the backseat of a limousine, but his entire plan is laid terrifyingly bare on election night. In lieu of an acceptance speech, Bob stands in front of his Charles Foster Kane-esque portrait and lets loose with the maniacal laughter. It’s chilling, and brilliantly captured by Mark Kirland’s direction and Grammer’s vocal performance.


Bob’s election is a strange pivot point in the episode, which enters the commercial break as a Springfield-set Face In The Crowd/Bob Roberts affair and comes out the other end as an All President’s Men riff. Drunk with the power he believes to be his birthright, Sideshow Bob sets about ruining life for the Simpsons: he demotes Bart to kindergarten, then threatens to knock down 742 Evergreen Terrace to make room for the long-promised Matlock Expressway. (Hey, there’s Face In The Crowd again!) If I have any major problems with “Sideshow Bob Roberts,” they’re based in its switching gears from character-driven piece to story-driven thriller. Then again, the show is called The Simpsons, so the final acts of the episode had to give Bart and Lisa something to do beyond bemoaning Bob’s win. At least the big twist—Bob’s well-documented voter-fraud scheme involves stuffing the voter logs with the dead, human and animal alike—has major emotional implications for Lisa. Springfield’s littlest liberal is incensed that the Terwilliger campaign would make her dead cat vote republican. Bart’s reaction to Lisa taking this slight personally is priceless.


But what’s also priceless is the window into Sideshow Bob’s psyche that’s gained from “Sideshow Bob Roberts.” Over the course of four appearances in six seasons, Kelsey Grammer has managed to shape his wild-haired, big-footed snob into a full-fledged character, one with motivations beyond an obsession with killing Bart. No, as that climactic courtroom showdown displays, Robert Underdunk Terwilliger’s mania for controlling the fates of other people extends to the whole of humanity. Ironically, he’s chosen to align himself with a political party that’s campaigned on a platform of limiting the government’s power to do such things for the past two decades—but he’s a crazy person, so he’ll take any side that will have him (controlling other people’s fates, especially if that fate is Bart’s).

And that’s as damning as political gibes get. From the series that brought you “I’ve said it before and I’ll say it again: Democracy simply doesn’t work,” “Sideshow Bob Roberts” indicts all sides of the political equation. The episodes targets are the people pulling the lever without knowing why they’re pulling it as well as the politicians who’ll say anything (and do all manner of circus tricks) to get a few extra levers to flip. In one of its most razor-sharp installments, The Simpsons gives itself plenty of satirical quarries, and bags nearly every one of them.


Stray observations:

  • This was probably unintentional on the part of the writers, but I love the parallel construction of and phonetic similarities between the candidates’ nicknames: “Diamond Joe” vs. “Sideshow Bob”
  • That little “Remember Sideshow Bob?” sequence is an inelegant detour, but I’ll give it a pass. After all, the character had only appeared three other times up until this point.
  • The brilliant sobriquet “beardo” appears in this episode, and was later carried over to Mission Hill, created by credited “Sideshow Bob Roberts” writers Bill Oakley and Josh Weinstein. I asked Oakley via Twitter if they coined the term; here’s his response.
  • The Flintstones Dial Telephone was a real tie-in manufactured in the 1960s; no word on whether or not second Fred Henry Corden was replicating actual Flinstones Dial Telephone dialogue in “Sideshow Bob Roberts.”
  • This week in Simpsons signage: In large print: “SPRINGFIELD HALL OF RECORDS.” In small print: “NOT THE GOOD KIND OF RECORDS, HISTORICAL ONES”
  • Next week: Kyle Ryan (or someone who’s not Kyle Ryan) invites you up to “Treehouse Of Horror V.” If memory serves, that’s a ghoul one.

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